Man versus Machine: Crossword playing AI Dr. Fill falls in tournament

Video games are more often than not about pitting human minds against the minds of machines. In Tetris, the game is built to increase speed while randomly giving you objects to build and then tear down. It’s a visceral microcosm of the John Henry struggle. Call of Duty is fine-tuned to give you a rollercoaster of warfare so theatrically absurd that Ian Fleming would blush, and it does so by creating gauntlets of computer-brained aggressors who want to shoot you. It’s nice to know that, despite the advances made in AI development that occur on a daily basis these days, human beings are still better at some games than programs are. For example: We can still kick computers’ asses at crossword puzzles.

Matthew Ginsberg Ph.D., a noted AI expert who taught at Stanford, created Dr. Fill, a crossword-solving program that can solve simple puzzles in as little as one minute and harder puzzles in about three. That’s around half the time of the best human crossword puzzle solvers. Ginsberg brought Dr. Fill to compete in the American Crossword Puzzle Tournament in Brooklyn, New York last weekend where it competed amongst 600 contestants. How did mankind stack up? Dr. Fill finished 141st.

“If I’m unlucky, I’ll end up 150th,” Ginsberg told The New York Times ahead of the tournament. He wasn’t. In a follow up article, Ginsberg explained that it was humorous clues and strange answers like needing to spell words backwards that flummoxed the AI. Beating Dr. Fill required trickier tactics then manipulating Mega Man 2‘s robot masters into a pattern loop, but the effect was the same.